Retusin

Base Information

• Chemical Name: Retusin
• CAS No.: 1245-15-4
• Molecular Formula: C19H18 O7
• Molecular Weight: 358.348
• Hs Code.: 2914509090
• European Community (EC) Number: 214-991-4
• NSC Number: 618937,61837
• UNII: M8591903SD
• DSSTox Substance ID: DTXSID60924839
• Nikkaji Number: J146.440J
• Wikipedia: Retusin_(flavonol)
• Wikidata: Q7317388
• Pharos Ligand ID: UNZA53N9646W
• Metabolomics Workbench ID: 25853
• ChEMBL ID: CHEMBL77966
• Mol file: 1245-15-4.mol

Synonyms:5-hydroxy-3,7,3',4'-tetramethoxyflavone

Chemical Property of Retusin

Chemical Property:

• Vapor Pressure: 1.48E-13mmHg at 25°C
• Melting Point: 156-161°C
• Boiling Point: 569.2°Cat760mmHg
• Flash Point: 205.6°C
• PSA: 87.36000
• Density: 1.36g/cm³
• LogP: 3.20000
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 358.10525291
• Heavy Atom Count: 26
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Retusin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC

Technology Process of Retusin

There total 35 articles about Retusin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

pentamethyl quercetin (1247-97-8) → retusin (1245-15-4)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.01.023

Reference yield: 86.0%

dimethylsulfide (75-18-3) + quercetol (117-39-5,74893-81-5) → retusin (1245-15-4)

Guidance literature:

With potassium hydroxide; In water; acetone;

DOI:10.1002/mrc.2510

Reference yield: 74.0%

quercetol (117-39-5,74893-81-5) + dimethyl sulfate (77-78-1) → retusin (1245-15-4)

Guidance literature:

With triethylamine; In acetone; at 0 - 60 ℃; for 3.08333h;

upstream raw materials:

diazomethane

1,4-dioxane

diethyl ether

quercetol

Downstream raw materials:

2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one

hexa-O-methylogossypetin

3,3',4',7-tetramethoxy-5-hydroxyflavothione

Refernces

• 1、 Herzig. "-". . p. 889. Retrieved 1885.
• 2、 Gomm,Nierenstein. "-". . p. 4408. Retrieved 1931.
• 3、 Li, Xue-Li,Zhang, Yan-Hua,Wang, Cai-Fang,Wang, Qiu-An. "Synthesis and antiproliferative activities of aminoalkylated polymethoxyflavonoid derivatives". . p. 1 - 8. Retrieved 2017.
• 4、 Ramos, Ingrid T. L.,Silva, Tania M. S.,Camara, Celso A.. "Synthesis of new 6- and 8-Alkenyl-3,7,3’,4’-Tetramethoxyquercetin derivatives by microwave-assisted Heck coupling". . p. 2583 - 2589. Retrieved 2019.
• 5、 Karimova,Baltina,Spirikhin,Sapozhnikova,Gabdrakhmanova,Makara. "Methylation of Quercetin by Diazomethane and Hypoglycemic Activity of its Tetra-O-Methyl Ether". . p. 837 - 841. Retrieved 2020.
• 6、 Chen, Hongping,Ding, Haiyan,Hu, Yuan,Li, Dan,Liu, Youping,You, Qiang. "Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma". . p. 12705 - 12716. Retrieved 2021/11/17.
• 7、 Rajaram, Pravien,Jiang, Ziran,Chen, Guanglin,Rivera, Alyssa,Phasakda, Alison,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong. "Nitrogen-containing derivatives of O-tetramethylquercetin: Synthesis and biological profiles in prostate cancer cell models". . p. 227 - 239. Retrieved 2019/03/23.